Best Vacation Rentals in The Berkshires

Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities. The Vacation Village in the Berkshires ideally places guests only moments away from a variety of activities, historical sites and delicious dining options. Biking trails, top-rate ski trails, fishing and swimming are all nearby. Guests can also enjoy the variety of amenities available at the Berkshires Village. The property features a state-of-the-art fitness center, private balconies and patios and fully and partially equipped kitchens. Jiminy Peak Mountain Ski Resort is 1.6 mi away from this hotel.

- "Perfect family getaway." - "This is the third time I’ve stayed here and it won’t be the last! Such an amazing place for a quick getaway!" - "Over all was a beautiful stay even though the shower was cold ." - "I love everything about my stay, particularly fireplace electric though but looks very real and super warm!" - "It was excellent as always!" - "Excellent" - "Great week all around!" - "Always a great time at VV. Grandchildren love it."

Hotel with free parking, steps from Williams College
Along with a restaurant, this smoke-free hotel has a fitness center and a bar/lounge. Free WiFi in public areas and free self parking are also provided. Other amenities include a conference center, a coffee shop/cafe, and coffee/tea in a common area.
The Williams Inn offers 64 air-conditioned accommodations with safes and bathrobes. Flat-screen televisions are featured in guestrooms.

Bathrooms include bathtubs or showers and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is provided daily.

- "Love the Williams Inn" - "Always great!" - "The room was excellent. The staff was great. The food was exceptional," - "Perfectly located close to the college, restaurants, shopping, and museums. Friendly staff, quiet setting, comfortable rooms, and good bar/restaurant. " - "The best hotel." - "super cute hotel, everything was in great condition, The BArn was delicious" - "Great locale, very nice restaurant, great design/interiors. Staff was always helpful and friendly. Will definitely go back next time we visit the north half of the Berkshires."

Featuring an indoor swimming pool and a fitness center, Berkshire Mountain Lodge is located in Pittsfield. Free WiFi access is available in this lodge. A full kitchen, sofa bed and flat-screen cable TV are included in each guest room. The private bathrooms are equipped with a hairdryer and free toiletries. Guests at the Pittsfield Berkshire Mountain Lodge can relax in the hot tub. A games room is also available. Berkshire Museum is 6 minutes’ drive from the lodge. Barrington Stage Company: Mainstage is 7 minutes’ drive. Tanglewood is 11 minutes' drive from the lodge.

- "For the price and location it was amazing" - "Great stay as always! Staff was welcoming and friendly and the unit was clean and comfortable and met our expectations." - "This is our 3rd year here and we think the staff is friendly and outstanding." - "Just right for winter getaway" - "Cozy clean and comfortable" - "Exceptional Stay Quiet Comfortable and cozy!" - "Affordable. Could be cleaner." - "Bad beginning. Did not honor agreed on price."

Hotel with free breakfast, a quick walk to The Mount
This smoke-free hotel features coffee/tea in a common area, concierge services, and a library. Free on-the-go breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, wedding services, a garden, and a picnic area are onsite.
Seven Hills Inn offers 45 air-conditioned accommodations with coffee/tea makers and hair dryers. Televisions come with satellite channels.

Bathrooms include bathtubs or showers with deep soaking bathtubs and complimentary toiletries. Business-friendly amenities include phones along with free local calls (restrictions may apply).

- "Loved the fact there was a fire pit and outdoor games. Beautiful setting." - "The Seven Hills Inn and the Mount are of the same era and are within walking distance. One of them has been converted into a B&B with very affordable room rates when booking in the Terrace House. In the shoulder season, we paid merely $150 on Expedia. Best of all you get to enjoy the garden terrace for breakfast and the lobby at the former mansion." - "This is a manor house with rooms in another building. Administration, lobby, and breakfast are in the manor house. It has an older world charm"

This bed and breakfast in the scenic Berkshires features uniquely styled guest rooms, each with a private bathroom. Hiking and bicycle trails in Kennedy Park are just 1 mile away. Rooms at the The Dewey by The Lenox Collection feature free Wi-Fi access and a seating area. They are decorated in bright colors, wood floors, and plush bedding. Select rooms have a fireplace or a TV. Guests can relax on the large terrace or in the library at the The Dewey by The Lenox Collection B&B. Conceirge services and daily newspapers are also available. Continental breakfast with local, in-season produce is served every morning. Tanglewood Musical Center is 5 minutes’ drive from the inn. Edith Wharton’s Estate, The Mount, is 2 miles away.

- "This brief getaway has been relaxing and most enjoyable." - "Just what you would imagine a New England Inn would offer." - "Lovely room, comfortable and quiet," - "good room but a negative regarding lack of staff and no coffee maker in room" - "Fabulous location but not good value for money overall" - "Part of the experience of old inn is the charm and a component to the charm is usually the staff. I was surprised at th"

While you're here, you can enjoy all the comforts of home and more, including an oven and a stovetop, as well as a dishwasher and free WiFi. Other amenities include laundry facilities, a freezer, towels, and an electric kettle.

- "Everything was Great" - "This place is very clean" - "Easy check in. Carmen was awesome. Close to stores, cafes and pet friendly." - "Great stay. Easy check-in. Comfortable." - "Our stay was perfect we will stay every time we come to town from now on Carmen is so friendly and accommodating such a great stay! Thank you" - "Cleanliness and comfort ranked very high here. We very much enjoyed the comfortable, large king bed and the cushy living room sofa. The unit was the size of a small apartment with large rooms having lots of windows and light including a large balcony with chairs - views of green leafy trees from some windows and town views from others (such as a parking lot etc. but expected being in downtown). It has a kitchen with all of the standard large and basic small appliances and all were clean and in working order. If you don’t want or need to cook in the kitchen, there are a couple of eateries within close walking distance with others at further walking/driving distances. During our two night mid week stay it was very quiet even though the Inn is off of a very busy local street. This property looks to be well used over many years and is kept to a relatively high standard of cleanliness and comfort. We had never used this type of remote check in/keyless service but it worked very well. At one point, I had to contact the Inn via phone and was able to speak with someone right away. I would not hesitate to stay here in the future. "

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk offers accommodations in Hancock, 20 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center. With mountain views, this accommodation provides a swimming pool. Rensselaer Polytechnic Institute is 27 miles away and Bennington Battle Monument is 29 miles from the apartment. With free Wifi, this 1-bedroom apartment features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave. Towels and bed linen are available in the apartment. The accommodation is non-smoking. Dining options are available close to the apartment. Tanglewood is 21 miles from WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk, while Norman Rockwell Museum is 27 miles from the property. Albany International Airport is 34 miles away.

- "Wonderful place- would definitely stay again!" - "Great location!! Very cozy newly renovated suite. Highly recommended" - "Wow! Indeed" - "Perfect spot for a comfortable stay!" - "Perfect home base for a ski trip!" - "Okay but won't be coming back."

Bed & breakfast in Lee with free breakfast and a 24-hour front desk
This bed & breakfast features an outdoor pool, a business center, and a meeting room. Free full breakfast is provided, as well as free WiFi in public areas, free self parking, and a free manager's reception. Additionally, concierge services, a 24-hour front desk, and a library are onsite.
Devonfield Inn B&B offers 11 air-conditioned accommodations with complimentary newspapers and complimentary bottled water. Accommodations offer separate sitting areas. Beds feature premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathtubs or showers with jetted bathtubs, bathrobes, complimentary toiletries, and hair dryers. This Lee bed & breakfast provides complimentary wired and wireless Internet access. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "The classic character of the Inn is so beautiful and adds to the whole experience!" - "It was a great last minute trip. The property is very well maintained and decorated for the holidays. I wish Doug and Tim a great holiday season and Happy New Year. We will be back!!" - "A really amazing property tucked away in a hidden gem of a town. The house itself is just amazing, a very cozy stay. Our bed was the most comfortable and calming with a faint aroma of strawberries everytime I turned over. I can’t wait to go back."

21 miles from Cranwell Spa & Golf Club in Hancock, Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort provides accommodations with access to a fitness center. With mountain views, this accommodation features a swimming pool. Tanglewood Musical Center is 21 miles from the vacation home and Tanglewood is 21 miles away. With free Wifi, this 3-bedroom vacation home offers a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Guests can also relax in the garden. Norman Rockwell Museum is 27 miles from the vacation home, while Rensselaer Polytechnic Institute is 28 miles away. Albany International Airport is 35 miles from the property.

- "Wonderful condo on Jiminy Peak and Great host - Howie." - "10/10 stay for you, your family/friends and pet" - "Fantastic weekend at Jiminy Peak!" - "Howie was very accommodating. We will definitely go back the grand kids loved it." - "My family loved the comfort of your condo" - "Lovely stay for our family. Thank you!" - "The villa was in a fantastic location & had all the conveniences we were looking for our getaway🍁🍂"

Bed & breakfast with free parking, in the vicinity of Ski Butternut
This smoke-free bed & breakfast features coffee/tea in a common area, concierge services, and express check-in. Free WiFi in public areas and free self parking are also provided. Other amenities include express check-out.
The Barrington offers 7 accommodations with complimentary bottled water and coffee/tea makers. These individually decorated accommodations have separate sitting areas and include desks. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include bathrobes, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and portable fans. Housekeeping is provided daily.

- "Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. " - "As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!" - "We absolutely loved our stay at The Barrington. The staff is lovely. The room was huge, beautiful and quiet. The breakfast was incredible. We will definitely be back. "

Devonfield Inn in Lee provides accommodations with a garden, a terrace, and a shared lounge. Featuring a seasonal outdoor swimming pool, the 4-star bed and breakfast has air-conditioned rooms with free Wifi, each with a private bathroom. The accommodation features a shared kitchen, luggage storage space, and organizing tours for guests. At the bed and breakfast, each unit has a flat-screen TV with cable channels. Guests at the bed and breakfast will be able to enjoy activities in and around Lee, like fishing and hiking. Skiing and cycling can be enjoyed nearby, while a ski pass sales point and ski storage space are also available on-site. Cranwell Spa & Golf Club is 3.8 miles from Devonfield Inn, while Norman Rockwell Museum is 5.7 miles from the property. Bradley International Airport is 50 miles away.

- "DOUG and JIM will make you feel at home right away. They will make you feel comfortable about traveling the area and giv" - "A fantastic experience ... everything you would want a B&B to be"

Bed & breakfast in Lee with free breakfast and a 24-hour fitness center
An outdoor pool, a 24-hour fitness center, and spa services are available at this smoke-free bed & breakfast. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a microwave in a common area, a refrigerator in a common area, and a seasonal outdoor pool are onsite.
The Inn at Stockbridge offers 14 air-conditioned accommodations with designer toiletries and hair dryers. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Flat-screen televisions come with cable channels.

This Lee bed & breakfast provides complimentary wired and wireless Internet access. Additionally, rooms include irons/ironing boards and complimentary toiletries. Housekeeping is provided daily.

- "Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 " - "Fantastic!" - "Well-run and elegant property. " - "We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"

22 miles from Tanglewood Musical Center in Hancock, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak provides accommodations with access to a hot tub. This property offers access to a pool table. There's a sun terrace and guests can use free Wifi and free private parking. Offering a patio and mountain views, the spacious vacation home includes 6 bedrooms, 3 living rooms, flat-screen TV, an equipped kitchen, and 6 bathrooms with a hot tub and a bath. Featuring air conditioning, this unit has a dressing room and a fireplace. The vacation home offers bed linen, towels, and laundry service. There is an on-site bar. For guests with children, the vacation home offers outdoor play equipment and a baby safety gate. Skiing, fishing, and hiking are possible within the area, and Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak offers ski storage space. Tanglewood is 23 miles from the accommodation, while Cranwell Spa & Golf Club is 23 miles from the property. Albany International Airport is 32 miles away.

- "Excellent retreat for large groups or multi-family get aways. We will return again in the future." - "Super excellent, highly recommended!!" - "The place is amazing! It gives us a very enjoyable vacation." - "We had and enjoyable and relaxing experience!" - "Beautiful, large home!" - "Thank you so much for such a nice place to stay. We had time for a nice campfire on final night."

Inn with free breakfast, near Questing
A restaurant, a bar/lounge, and a coffee shop/cafe are available at this inn. Free continental breakfast is provided, as well as free WiFi in public areas, free self parking, and a free manager's reception. Additionally, a seasonal outdoor pool, a meeting room, and a garden are onsite.
The Old Inn On The Green offers 11 air-conditioned accommodations with hair dryers and complimentary toiletries. Rooms open to balconies or patios. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Televisions come with cable channels. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.
Recreational amenities at the inn include a seasonal outdoor pool.

- "It was great experience. " - "Everything was wonderful - the food was delicious and the staff very attentive at dinner. The only thing that was a bit off-putting was that there were two leftover red wine glasses left out on the table on the balcony that we wished had been removed before our arrival, but that's just a little thing. " - "What a wonderful experience, including the exceptional restaurant!" - "Built in 1750, The Old Inn On The Green is a rare and remarkable testament to colonial America, Under the deft leadership of owner Peter Platt with the meticulous guidance of his superlative dining manager, Eric, the Inn offers an authentic bygone-era dining and lodging experience unlike any other. From the moment you step inside, you are transported back to the 18th century. The inn’s structure, largely untouched by time, is steeped in history, with its original wooden beams and creaking floorboards preserving the aura of its storied past. But perhaps what sets the atmosphere apart is the dining room— menu changes with the seasons, reflecting the bounty of the surrounding area. Exquisite dishes of finely roasted, richly-flavored choice meats in velvety sauces takes you back to the days when hunters supplied the village of New Marlborough with game. Fresh fish and seafood delicacies from New England’s fabled coastal fishing fleet are transformed into succulent briny ocean masterpieces that would rival any Michelin-starred restaurant in New York or Paris. The inn offers authentic 18th-century coach house accommodations that further immerse guests in the past. Each room is meticulously furnished with period-appropriate decor, from wood hewed beds draped in fine linens to hand-crafted wooden chests and writing desks. The Old Inn is not just a place to eat and sleep—it is an experience, a living museum of New England’s colonial past. HIGHLY RECOMMENDED!! "

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor offers accommodations in Hancock, 20 miles from Cranwell Spa & Golf Club and 21 miles from Tanglewood Musical Center. With mountain views, this accommodation provides a swimming pool. Tanglewood is 21 miles away and Norman Rockwell Museum is 27 miles from the apartment. With free Wifi, this 1-bedroom apartment offers a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the apartment. The accommodation is non-smoking. Rensselaer Polytechnic Institute is 27 miles from the apartment, while Bennington Battle Monument is 29 miles from the property. Albany International Airport is 34 miles away.

Wellness Facilities • Internet • Security/Safety • Fireplace/Heating • Accessibility • Pool

Adults-only bed & breakfast in Lenox with free breakfast
Along with coffee/tea in a common area, this smoke-free bed & breakfast has express check-in and express check-out. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a lobby fireplace.
33 Main offers 8 air-conditioned accommodations with bathrobes and hair dryers. Each accommodation is individually decorated. Beds feature premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include showers and complimentary toiletries. Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Additionally, rooms include irons/ironing boards and portable fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

- "33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! " - "Clean room, gracious host." - "Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. " - "Love this!" - "I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"

Summer and Fall in Sheffield with Monthly Special Pricing Available offers accommodations in Sheffield, 22 miles from Tanglewood Musical Center and 22 miles from Tanglewood. The air-conditioned accommodation is 22 miles from Cranwell Spa & Golf Club. Free Wifi is available throughout the property and Norman Rockwell Museum is 17 miles away. The spacious vacation home includes 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, as well as a kettle. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests at the vacation home can enjoy skiing and cycling nearby, or make the most of the outdoor pool. Great Falls is 9.2 miles from Summer and Fall in Sheffield with Monthly Special Pricing Available, while Canaan Village Historic District is 9.4 miles from the property. Bradley International Airport is 44 miles away.

Air Conditioner • Pool • Internet • Other • Skiing • Fireplace/Heating • Security/Safety • Pet Friendly • Barbecue/Outdoor Cooking • Sports/Activities • Child Friendly

Hotel in Lenox with a seasonal outdoor pool and a bar
This hotel features a bar/lounge, an outdoor tennis court, and a seasonal outdoor pool. Free WiFi in public areas and free self parking are also provided. Additionally, concierge services, a library, and express check-in are onsite.
Hampton Terrace Inn offers 14 air-conditioned accommodations with complimentary bottled water and irons/ironing boards. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Flat-screen televisions come with cable channels. This Lenox hotel provides complimentary wireless Internet access. Housekeeping is provided daily.
Recreational amenities at the hotel include an outdoor tennis court and a seasonal outdoor pool.

- "Beautiful historic house in a great location. Responsive owner. Great visit!" - "My husband and I stayed at the Hampton Terrace Inn for 2 nights this September. We were looking for safe place to stay during these unfortunate COVID-19 pandemic times, with the option of separate lodging. We therefore stayed in one of the cottage suites which we found to be large, comfortable, quiet, and well-appointed. Our cottage had a gas fireplace, which was very lovely and warmed up the room rather quickly. Stan the owner, was an excellent host. He was very proactive in communicating with us after our booking and checking in with us constantly to ensure that we were comfortable or to see if we needed anything. We were also fortunate enjoy the sumptuous breakfast, offered at the Inn which was truly fabulous. The Inn also offers a bar, where you can enjoy cordials and has a Keurig machine for making coffee or tea in the room. The Inn is centrally located, walking distance to all the good restaurants in Lenox: Alta, Brava and Zinc! There is ample and convenient parking within the compound. We were very happy and content during our stay and highly recommend the place for a wonderful, low-key and comfortable stay. "

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires offers accommodations in Stockbridge, 3.7 miles from Norman Rockwell Museum and 6.9 miles from Cranwell Spa & Golf Club. This vacation home provides air-conditioned accommodations with a patio. Tanglewood Musical Center is 7.1 miles away and Tanglewood is 7.3 miles from the vacation home. With free Wifi, this 3-bedroom vacation home offers a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. Great Falls is 19 miles from the vacation home, while Canaan Village Historic District is 19 miles from the property. Albany International Airport is 49 miles away.

Pet Friendly • Parking • Internet • Fireplace/Heating • Security/Safety • View • Air Conditioner

While you're here, you can enjoy all the comforts of home and more, including a heated pool and a refrigerator, as well as a stovetop and free WiFi. Other amenities include laundry facilities, a freezer, towels, and a DVD player.

- "We loved our stay at the Villages, our apt. was very comfortable, with a beautiful view of the mountains. I especially loved the indoor pool, and outdoor spa tub. Service on checkin was great. We will be back." - "We loved staying here felt just like home!" - "Clean, neat, comfortable units, grounds well cared for." - "We have stayed at this property since my kids were little. Many special memories here. It is always a clean and pleasant stay. The staff is helpful and courteous. Appreciate the complimentary, coffee, tea and hot cocoa and movie rental services. Hard to beat the proximity to Jiminy Peak. "